1-hydroxy-11-methoxycanthin-6-one - Compound Card

1-hydroxy-11-methoxycanthin-6-one

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1-hydroxy-11-methoxycanthin-6-one

Structure
Zoomed Structure
  • Family: Plantae - Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Canthinone Alkaloid
Canonical Smiles COc1cccc2c1c1c(O)cnc3c1n2c(=O)cc3
InChI InChI=1S/C15H10N2O3/c1-20-11-4-2-3-9-13(11)14-10(18)7-16-8-5-6-12(19)17(9)15(8)14/h2-7,18H,1H3
InChIKey PGCMCHVRXMXNSW-UHFFFAOYSA-N
Formula C15H10N2O3
HBA 5
HBD 1
MW 266.26
Rotatable Bonds 1
TPSA 63.83
LogP 2.15
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 266.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brucea antidysenterica Simaroubaceae Plantae 459111

Showing of synonyms

  • Makong YS, Fotso GW, et al. (2021). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae).. Natural product research,2021, 35(12), 2037-2043. [View] [PubMed]
Pubchem: 86132504
Nmrshiftdb2: 60078750

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)n4c2c(ccc4=O)ncc3

Level: 0

Mol. Weight: 266.26 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.190
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.430
Plasma Protein Binding
79.57
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.350
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.140
Rat (Acute)
2.210
Rat (Chronic Oral)
1.680
Fathead Minnow
4.690
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
485.190
Hydration Free Energy
-13.770
Log(D) at pH=7.4
1.440
Log(P)
1.49
Log S
-4.96
Log(Vapor Pressure)
-7.76
Melting Point
271.66
pKa Acid
9.54
pKa Basic
4.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9519
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.9429
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9405
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9190
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9172
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9059
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9032
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8934
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8884
Polyunsaturated fatty acid lipoxygenase ALOX15 P12530 LOX15_RABIT Oryctolagus cuniculus 3 0.8770
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8660
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8593
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8575
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8553
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8552
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8506
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8488
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8466
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8422
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8363
Stimulator of interferon genes protein Q3TBT3 STING_MOUSE Mus musculus 3 0.8339
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8293
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8276
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8200
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8113
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.8065
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8055
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.8053
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8021
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7984
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7948
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7942
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7925
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7906
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7900
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7899
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7863
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7833
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7799
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7798
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7781
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7765
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7754
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7739
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7727
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7695
1-deoxy-D-xylulose 5-phosphate reductoisomerase P9WNS1 DXR_MYCTU Mycobacterium tuberculosis 3 0.7681
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7652
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7639
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7581
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7581
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7545
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7525
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7509
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7506
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7499
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7490
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7465
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7443
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7430
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7421
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7381
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7365
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7345
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 3 0.7330
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7314
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7308
1-deoxy-D-xylulose 5-phosphate reductoisomerase P9WNS1 DXR_MYCTU Mycobacterium tuberculosis 3 0.7293
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7293
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7267
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7258
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7252
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7242
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7220
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7209
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7188
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7169
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7125
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7123
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7108
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7079
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7066
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7063
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7059
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7043
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7041
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7030
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7019
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7003
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7003

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